Acetonitrile → HCID 178454719, compound

HRID 386938Notes

Reaction equation

HRID 386938 reaction equation
C1C[C@H](C(O)=O)CC[C@H]1CN.[C:12]([O:17][CH:18]([O:20][C:21]([NH:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31]([OH:33])=[O:32])[CH2:27][CH2:26]1)=[O:22])[CH3:19])(=[O:16])[CH2:13][CH2:14][CH3:15].C(=O)(O)[O-].[Na+:38].C(#N)C>O>[C:12]([O:17][CH:18]([O:20][C:21]([NH:23][CH2:24][C@H:25]1[CH2:26][CH2:27][C@H:28]([C:31]([O-:33])=[O:32])[CH2:29][CH2:30]1)=[O:22])[CH3:19])(=[O:16])[CH2:13][CH2:14][CH3:15].[Na+:38]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 178454718HCID 178454718, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178454719HCID 178454719, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the general procedure for the formation of the corresponding sodium carboxylates of acyloxyalkyl carbamates of tranexamic acid, 946 mg (3.0 mmol) of trans-4-{[1-(butanoyloxy)ethoxycarbonyl]aminomethyl}-cyclohexanecarboxylic acid 10 was reacted with 252 mg (3.0 mmol) of sodium bicarbonate (NaHCO3) in 20 mL of a mixture of acetonitrile and water (1:1) to yield 1.02 g (quant.) of the title compound 11 as a colorless powder. 1H NMR (400 MHz, DMSO-d6): δ=0.73-0.84 (m, 2H), 0.87 (t, J=6.8 hz, 3H) 1.08-1.20 (m, 2H), 1.20-1.32 (m, 1H), 1.38 (d, J=5.2 Hz, 3H), 1.46-1.56 (m, 2H), 1.60-1.74 (br. m, 3H), 1.76-1.83 (br. m, 2H), 2.25 (t, J=7.2 Hz, 2H), 2.78 (t, J=6.0 Hz, 2H), 6.65 (q, J=5.2 Hz, 1H), 7.41 (t, J=5.6 Hz, 1H). MS (ESI) m/z 338.16 (M+Na)+; 314.18 (M−H)−.

Sources & evidence

ORD record
ord-383b6d51140c4430aee771b578fd26f1
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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